(Prop-2-en-1-yl)stannane → 5-Allyl-4-chloro-2-[2-(3,5-dimethylphenyl)-acetylamino]-benzoic acid methyl ester

HRID 1857631ノート

反応式

HRID 1857631 の反応式
[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[C:8](I)[C:7]([Cl:11])=[CH:6][C:5]=1[NH:12][C:13](=[O:23])[CH2:14][C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[CH:16]=1.[CH2:25]([Sn])[CH:26]=[CH2:27]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[C:8]([CH2:27][CH:26]=[CH2:25])[C:7]([Cl:11])=[CH:6][C:5]=1[NH:12][C:13](=[O:23])[CH2:14][C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[CH:16]=1

参加物

4

反応物 2

HCID 15842380(Prop-2-en-1-yl)stannaneHCID 540909164-Chloro-2-[2-(3,5-dimethylphenyl)-acetylamino]-5-iodo-benzoic acid methyl ester

生成物 1

HCID 542443075-Allyl-4-chloro-2-[2-(3,5-dimethylphenyl)-acetylamino]-benzoic acid methyl ester

試薬・触媒・溶媒 1

HCID 178418476HCID 178418476、化合物触媒

反応条件

温度
100 °C

実験手順

To a suspension of 4-chloro-2-[2-(3,5-dimethylphenyl)-acetylamino]-5-iodo-benzoic acid methyl ester (2.39 g in 12 mL N,N-dimethylformamide) and 0.183 g bis(triphenylphosphine)palladium(II) chloride was added 2.02 mL allyltin and the mixture heated to 100° C. on an oil bath. After 2 hours, the mixture was cooled, partitioned between ethyl acetate and water and the organic layer washed further with brine. Concentration of the dried (magnesium sulfate) organics and purification by flash chromatography on silica gel (hexane:ethyl acetate, 95:5; then 90:10) gave the title compound (1.4 g).

後処理

  1. temperaturethe mixture was cooled
  2. custompartitioned between ethyl acetate and water
  3. washthe organic layer washed further with brine
  4. dry with materialConcentration of the dried (magnesium sulfate) organics
  5. custompurification by flash chromatography on silica gel (hexane

出典と根拠

ORDレコード
ord-58a59c8f2fcc46ff9b510fc4194b8886
出典データセット
uspto-grants-2000_11
特許番号
US06147088

反応ノート

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